Expanding industrial applications of palladium catalysts

Synthesis (Germany)

Volumn 1990, Issue 9, 1990, Pages 739-749

  Tsuji, Jiro ^a  

^a OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85081225068     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-1990-27001     Document Type: Review

References (124)

1. Tsuji, J., Organic Synthesis with Palladium Compounds, Springer Verlag, Berlin, 1980.
2. Heck, R. F., Palladium Reagents in Organic Synthesis, Academic Press, Orlando, 1985.
3. Trost, B. M., Comprehensive Organometallic Chemistry, 1982, pp. 799.
4. Kusunoki, Y.; Okazaki, H. Hydrocarbon Process 1974, No. 11, 129.
5. Moiseev, I. I.; Vargaftik, M. N. Dokl. Akad. Nauk SSSR 1960, 133, 377.
6. Holzrichter, H.; Kroenig, W.; Frenz, B. German Patent 1185604(1962), Bayer
7. C. A. 1964, 60, 11902.
8. National Distillers, US Patent 3190912 (1962)
9. British Patent, 976613;
10. C. A. 1965, 62, 14505.
11. Nagato, N.; Maki, K.; Uematsu, T.; Ishioka, R., Japanese Patent Kokai 32747 (1985)
12. US Patent 4567292, Showa Denko K. K.;
13. C. A. 1986, 105, 152546.
14. Tamura, M.; Yasui, A. J. Chem. Soc., Chem. Commun. 1968, 1209.
15. Shell, US Patent 1029319 and 3349118 (1967).
16. Neth. Appl. 301 and 519 (1965);
17. C. A. 1966, 64, 6502.
18. Mitsubishi Kasei Corporation, CHEMTECH 1988, 759.
19. Pommer, H.; Nurrenbach, A. Pure Appl. Chem. 1975, 43, 527.
20. Lloyd, W. G.; Luberoff, B. J. J. Org. Chem. 1969, 34, 3949.
21. Matsui, K.; Uchiumi, S.; Iwayama, A.; Umezu, T. Japanese Patent Kokai 106635 (1982)
22. Eur. Patent Appl. EP 55108, Ube Industries. Ltd.;
23. C. A. 1982, 97, 162364.
24. Nakai, M.; Enomiya, T. Japanese Patent Kokai 128343 and 128344 (1984)
25. Eur. Patent Appl. EP 101223, Ube Industries, Ltd.;
26. C. A. 1984, 101, 54715.
27. Tsuji, J.; Morikawa, M.; Kiji, J. J. Am. Chem. Soc. 1964, 86, 8451.
28. Fenton, D. M.; Steinwand, P. J. J. Org. Chem. 1972, 37, 2034.
29. Olivier, K. L.; Biale, D. Hydrocarbon Processing 1972, No. 11, 95.
30. Yukawa, T.; Tsutsumi, S. J. Org. Chem. 1969, 34, 738.
31. Wada, K.; Hara, Y. Japanese Patent Kokai 71039(1981), 21342 (1982).
32. Wada, K.; Kobayashi, Y.; Kasori, Y. US Patent 4578507 (1986)
33. Eur. Patent Appl. EP. 152075, Mitsubishi, Kasei Corp.;
34. C. A. 1986, 104, 5645.
35. Umemura, S.; Matsui, K.; Ikeda, K.; Masunaga, K.; Kadota, T. Japanese Patent 35658 (1981)
36. German Patent (DOS) 2853178, Ube Industries, Ltd.;
37. C. A. 1979, 91, 123415.
38. Nishimura, K.; Furusaki, S.; Shiomi, Y; Fujii, K.; Nishihara, K.; Yamashita, M. Japanese Patent 35897 (1982)
39. Eur. Patent EP 77542, Ube Industries, Ltd.;
40. C. A. 1983, 99, 87654.
41. Uchiumi, S.; Ataka, K.; Sataka, K. Japanese Patent Kokai 78146 (1984) and 120838 (1985)
42. Eur. Patent Appl. EP 108332, Ube Industries, Ltd.;
43. C. A. 1984, 101, 90431.
44. van Helden, R.; Verberg, G. Rec. Trav. Chim. 1965, 84, 1263.
45. Davidson, J. M.; Triggs, C. Chem. Ind. (London) 1966, 457.
46. Shiotani, A.; Itatani, H.; Inagaki, T. J. Mol. Catal. 1986, 34, 57.
47. Kominami, N.; Tamura, N.; Yamamoto, E. Japanese Patent 34542-34548(1975), Asahi Chemical Co.;
48. C. A. 1976, 84, 150339 and 150340.
49. Bryant, D. R.; MeKeon, J. E.; Ream, B. C. J. Org. Chem. 1968, 33, 4123, and 1969, 34, 1106.
50. Matsuda, T; Shirafuji, T. Japanese Patent Kokai 151135 and 151136(1977), Sumitomo Chemical Co. Ltd.;
51. C. A. 1978, 88, 120772 and 1979, 90, 54650.
52. Tsuji, J.; Iwamoto, N. J. Chem. Soc., Chem. Commun. 1966, 380.
53. Fenton, D. M.; Steinwand, P. J. J. Org. Chem. 1974, 39, 701.
54. Uchinmi, S.; Yamashita, M. J. Jpn Petrol. Inst. 1982, 25, 197.
55. Japanese Patent Kokai 813 (1978)
56. German Patent (DOS) 2838856 and 2733730;
57. C. A. 1979, 91, 4958 and 1978, 88, 152047.
58. Hallgren, J. E.; Lucas, G. M.; Mattews, R. O. J. Organometal. Chem. 1981, 204, 135, and 1974, 175, 135.
59. Fukuoka, S.; Chono, M.; Kohno, M. J. Org. Chem. 1984, 49, 1458
60. CHEMTECH, 1984, 670.
61. Hardy, W. B.; Bennett, R. P. Tetrahedron Lett. 1967, 961.
62. Zajacek, J.; McCoy, J. J. US Patent 3993685(1976), Atlantic Richfield:
63. C. A. 1977, 56, 89440.
64. Smidt, J.; Hafner, W.; Jira, R.; Sieber, R.; Sedlmeier, J.; Sabel, A. Angew. Chem. 1963, 74, 93.
65. Kawamoto, R; Tanaka, S.; Honma, Y. Japanese Patent 20290 and 26661(1982), 816 (1986)
66. US Patent 4425277, Shin Etsu Vinyl Acetate Co.;
67. C. A. 1984, 100, 120533.
68. Mizoroki, T; Mori, K.; Ozaki, A. Bull. Chem. Soc. Jpn. 1971, 44, 581.
69. Heck, R. F.; Nolley, J. P. J. Org. Chem. 1972, 37, 2320.
70. Chalk, A. J.; Magennis, S. A. J. Org. Chem. 1976, 41, 1206.
71. Melpolder, J. B.; Heck, R. F. J. Org. Chem. 1976, 41, 265.
72. Hallberg, A.; Westfelt, L.; Andersson, C. M. Synthetic Commun. 1985, 15, 1131.
73. Miyaura, N.; Yamada, K.; Suginome, H.; Suzuki, A. J. Am. Chem. Soc. 1985, 107, 972.
74. Kobayashi, Y; Shimazaki, T; Sato, F. Tetrahedron Lett. 1987, 28, 5849.
75. Cacchi, S.; Morera, E.; Ortar, G. Tetrahedron Lett. 1984, 25, 2271.
76. Scott, W. J.; Crisp, G. T.; Stille, J. K. J. Am. Chem. Soc. 1984, 106, 4630.
77. Farina, V.; Baker, S. R.; Sapiro, C. Tetrahedron Lett. 1988, 29, 6043.
78. Rich, J. D. J. Am. Chem. Soc. 1989, 111, 5886.
79. Blaser, H. U.; Spencer, A. J. Organometal. Chem. 1982, 233, 267 and 1984, 265, 323.
80. Cassar, L. J. Organometal. Chem. 1975, 93, 253.
81. Dieck, H. A.; Heck, R. F. J. Organometal. Chem. 1975, 93, 259.
82. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467.
83. Cruickshank, K. A.; Stochwell, D. L. Tetrahedron Lett. 1988, 29, 5221.
84. Robins, M. J.; Barr, P. J. J. Org. Chem. 1983, 48, 1854.
85. Yoshida, H.; Sugita, N.; Kudo, K.; Takezaki, Y. Nippon Kagaku Zasshi 1974, 1386.
86. Schoenberg, A.; Bartoletti, I.; Heck, R. F. J. Org. Chem. 1974, 39, 3318.
87. Hidai, M.; Hikita, X; Wada, Y.; Fujikura, Y.; Uchida, Y. Bull. Chem. Soc. Jpn. 1975, 48, 2075.
88. Ito, T.; Mori, K.; Mizoroki, T.; Ozaki, A. Bull. Chem. Soc. Jpn 1975, 48, 2091.
89. Stille, J. K.; Wong, P. K. J. Org. Chem. 1975, 40, 532.
90. Fuchikami, T.; Ojima, I. Tetrahedron Lett. 1982, 23, 4099.
91. Tsuji, J.; Takahashi, H.; Morikawa, M. Tetrahedron Lett. 1965, 4381.
92. Hata, G.; Takahashi, K.; Miyake, A. J. Chem. Soc., Chem. Commun. 1970, 1392.
93. Atkins, K. E.; Walker, W. E.; Manyik, R. M. Tetrahedron Lett. 1970, 3821.
94. Tsuji, J.; Shimizu, I.; Minami, I.; Ohashi, T.; Sugiura, T; Takahashi, K. J. Org. Chem. 1985, 50, 1523.
95. Hazato, A.; Tanaka, T.; Okamura, N.; Sakauchi, K.; Kurozumi, S. Japanese Patent Kokai 303962(1988), Teijin Co.
96. Shimizu, I.; Tsuji, J. J. Am. Chem. Soc. 1982, 104, 5844.
97. Kataoka, H.; Yamada, T; Goto, K.; Tsuji, J. Tetrahedron 1987, 43, 4107.
98. Tsuji, J.; Nisar, M.; Shimizu, I.; Minami, I. Synthesis 1984, 1009.
99. Tsuji, J.; Yamakawa, T. Tetrahedron Lett. 1979, 613.
100. Minami, I.; Ohashi, Y; Shimizu, I.; Tsuji, J. Tetrahedron Lett. 1985, 26, 2449.
101. Kunz, C; Univerzagt, C. Angew. Chem., Int. Ed. Engl. 1984, 23, 436.
102. Deziel, R. Tetrahedron Lett. 1987, 28, 4371.
103. Hayakawa, Y.; Kato, H.; Uchiyama, M.; Kajino, H.; Noyori, R. J. Org. Chem. 1986, 51, 2402.
104. Takahashi, S.; Shibano, T; Hagihara, N. Tetrahedron Lett. 1967, 2451.
105. Smutny, E. J. J. Am. Chem. Soc. 1967, 89, 6793.
106. Atkins, K. E.; Walker, W. E.; Manyik, R. M. J. Chem. Soc., Chem. Commun. 1971, 330.
107. Yoshimura, N.; Tamura, M. Japanese Patent 11114 (1988). Kuraray Co.
108. Rofia, P.; Gregorio, G.; Conti, F.; Fregalia, G. F.; Ugo, R. J. Organometal. Chem. 1973, 55, 405.
109. Tsuji, J.; Takahashi, M. J. Mol. Catal. 1981, 10, 107.
110. Billups, W. E.; Walker, W. E.; Shields, T. C. J. Chem. Soc., Chem. Commun. 1971, 1067.
111. Tsuji, J.; Mori, Y; Hara, M. Tetrahedron 1972, 28, 3721.
112. Drent, E.; van Goch, J. Eur. Patent Appl. EP 284170
113. British Patent, 8707405, Shell International Research;
114. C. A. 1989, 110, 39519.
115. Tsuji, J.; Yamakawa, T.; Kaito, M.; Mandai, T. Tetrahedron Lett. 1978, 2075.
116. Kumobayashi, H.; Mitsuhashi, S.; Akutagawa, S.; Otsuka, S Chem. Lett. 1986, 157.
117. Tsuji, J.; Morikawa, M.; Kiji, J. Tetrahedron Lett. 1963, 1437.
118. Bittler, K.; Kutepow, N. V.; Neubauer, K.; Reis, H. Angew. Chem. 1968, 80, 352
119. Angew. Chem. Int. Ed. Engl. 1968, 7, 359.
120. Takeda, M.; Uchide, M.; Iwane, H. Japanese Patent Kokai 51338 (1977) and 18533 (1978)
121. German Patent (DOS) 2646792, Mitsubishi Petrochemical Co.;
122. C. A. 1977, 87, 67848.
123. Drent, E. Eur. Patent Appl. EP 121965 and 253416, Shell International Research;
124. C. A. 1985, 102, 46423 and 1988, 109 7119.